Enterprise Price-Ceiling Discovery
Keep asking for more until deals break; losing 20-30% to price is how you find the ceiling.
- Difficulty
- Moderate
- Time to result
- ~weeks to results
- Steps
- 3
- Confidence
- 88%
A tactic for enterprise deals where the true willingness to pay is unknown. Because most companies are dramatically underpriced, you should keep pushing price upward in live conversations and accept that losing some deals on price is the feedback that reveals your ceiling. Zero hesitation from a buyer means you left money on the table.
Origin
Drawn from Naomi Ionita's work with Menlo portfolio company Envoy and founder Larry Gadea's story of 10x-ing a quote in a live sales meeting.
Core principles
- 01The vast majority of companies are undercharging, so the default bias should be to ask for more
- 02Instant acceptance with no hesitation is a signal you priced too low
- 03Losing roughly 20-30% of deals to price is a healthy sign you are probing the true ceiling
How to run it
- 1
Read the room and push the quote
In a warm enterprise conversation where the prospect is leaning in, ask for meaningfully more than your typical price rather than defaulting to your standard rate.
Pro tip Ionita suggests incrementing (2-3x) rather than jumping straight to 10x, so you preserve data points about where resistance begins.
Watch out Jumping straight to 10x can win but tells you nothing about the true ceiling because you skipped the resistance signal.
- 2
Treat zero hesitation as underpricing
If the buyer says yes with no pause, you have not found the ceiling. Note it as evidence you can push further next time.
Watch out No hesitation is not a win to celebrate — it is a warning you are underpriced.
- 3
Push until deals break, then hold near that line
Keep raising until you lose deals on price. Losing on the order of 20-30% of deals is reasonable and tells you where the limit is.
Pro tip Every price point is a feedback loop; you need enough data points across segments to optimize, so don't over-index on a single deal.
Watch out Without enough data points across distinct segments you cannot tell a true ceiling from a one-off outlier.
In the wild
In a meeting with a big hospitality company that was leaning in and excited, Envoy founder Larry Gadea decided in the moment to ask for 10x his typical price. The exec said 'okay sure, sounds good' without a second of hesitation.
→ Gadea learned he was wildly underpriced and had never considered the ceiling; the zero hesitation implied he could have pushed even further.
Common mistakes
Anchoring to your typical price in warm deals
Most companies are underpriced, so quoting your standard rate to an enthusiastic enterprise buyer systematically leaves large amounts on the table.
Fearing any lost deal on price
Never losing on price means you never found the ceiling; a reasonable 20-30% loss rate is the feedback that locates the true limit.
Is it for you?
Best for
Founders running enterprise or high-touch sales who suspect they are underpriced
Not ideal for
Self-serve PLG pricing pages, where you experiment via controlled tests rather than live negotiation
From the transcript
“he decided to 10x the price that he was typically charging people so just in the moment he said just go for it go out…”
“what I encourage users to do in um especially in like these Enterprise conversations is to continue to ask for more to understand where the…”
“imagine it's strategically smarter not to go straight to 10x and maybe go 2 or 3x until people start pushing back because you lose a…”
From the episode
How to price your product
Naomi Ionita (Menlo Ventures)